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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of fluorinated spiro-1,3-oxazines and thiazines via Selectfluor-mediated intramolecular cyclization
Chinu Gogoi1,2, Ujwal Pratim Saikia3, Priyam Borah1
1Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat-785006, Assam, India. ppahari@gmail.com.
Abstract:
A fluorination-induced intramolecular cyclization for the synthesis of fluoro-substituted spiro-1,3-oxazine and spiro-1,3-thiazine derivatives is described. N-(2-(Cyclohex-1-en-1-yl)ethyl)benzamide and benzothioamide are used as the substrates, and the cationic fluorinating agent Selectfluor works as the fluoride source. The reaction yields a single diastereomer. The scope of this regioselective fluorination reaction is established by preparing thirty different spirooxazine and spirothiazine derivatives.
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